IES980552A2 - Improved process for preparing N-phosphonomethyl iminodiacetic acid - Google Patents
Improved process for preparing N-phosphonomethyl iminodiacetic acidInfo
- Publication number
- IES980552A2 IES980552A2 IE980552A IES980552A IES980552A2 IE S980552 A2 IES980552 A2 IE S980552A2 IE 980552 A IE980552 A IE 980552A IE S980552 A IES980552 A IE S980552A IE S980552 A2 IES980552 A2 IE S980552A2
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- pmida
- alkali metal
- iminodiacetic
- metal salt
- Prior art date
Links
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 41
- -1 alkali metal salt Chemical class 0.000 claims abstract description 30
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 30
- 239000011707 mineral Substances 0.000 claims abstract description 30
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 27
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 20
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 11
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000012429 reaction media Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 19
- 150000003839 salts Chemical class 0.000 abstract description 13
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000005562 Glyphosate Substances 0.000 abstract description 2
- 229940097068 glyphosate Drugs 0.000 abstract description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229910001868 water Inorganic materials 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 16
- 230000000717 retained effect Effects 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 235000012970 cakes Nutrition 0.000 description 14
- 239000012065 filter cake Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical compound [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 description 8
- 235000019256 formaldehyde Nutrition 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 235000021463 dry cake Nutrition 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE980552A IES980552A2 (en) | 1998-07-09 | 1998-07-09 | Improved process for preparing N-phosphonomethyl iminodiacetic acid |
| TW088111544A TWI243822B (en) | 1998-07-09 | 1999-07-07 | Improved process for preparing N-phosphonomethyl iminodiacetic acid |
| CN99808354.2A CN1221557C (zh) | 1998-07-09 | 1999-07-08 | 制备n-膦酰基甲基亚氨基二乙酸的方法 |
| AU46430/99A AU761569B2 (en) | 1998-07-09 | 1999-07-08 | Process for preparing N-phosphonomethyl iminodiacetic acid |
| DE69916067T DE69916067T2 (de) | 1998-07-09 | 1999-07-08 | Verfahren zur herstellung von n-phosphonomethyl iminodiessigsäure |
| ARP990103344A AR019356A1 (es) | 1998-07-09 | 1999-07-08 | Procedimiento para preparar acido n-fosfonometil-iminodiacetico (pmida), |
| EP99929654A EP1095048B1 (en) | 1998-07-09 | 1999-07-08 | Process for preparing n-phosphonomethyl iminodiacetic acid |
| AT99929654T ATE263175T1 (de) | 1998-07-09 | 1999-07-08 | Verfahren zur herstellung von n-phosphonomethyl iminodiessigsäure |
| BR9911949-8A BR9911949A (pt) | 1998-07-09 | 1999-07-08 | Processo para preparar ácido iminodiacético de n-fosfonometila |
| MYPI99002874A MY125042A (en) | 1998-07-09 | 1999-07-08 | Improved process for preparing n-phosphonomethyl iminodiacetic acid |
| CA002337111A CA2337111A1 (en) | 1998-07-09 | 1999-07-08 | Process for preparing n-phosphonomethyl iminodiacetic acid |
| US09/743,380 US6515168B1 (en) | 1998-07-09 | 1999-07-08 | Process for preparing N-phosphonomethyl iminodiacetic acid |
| PCT/IE1999/000062 WO2000002888A1 (en) | 1998-07-09 | 1999-07-08 | Process for preparing n-phosphonomethyl iminodiacetic acid |
| IDW20010303A ID27785A (id) | 1998-07-09 | 1999-07-08 | Proses pembuatan asam n-fosfonometil iminodiasetat |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE980552A IES980552A2 (en) | 1998-07-09 | 1998-07-09 | Improved process for preparing N-phosphonomethyl iminodiacetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IES980552A2 true IES980552A2 (en) | 1999-08-11 |
Family
ID=11041846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE980552A IES980552A2 (en) | 1998-07-09 | 1998-07-09 | Improved process for preparing N-phosphonomethyl iminodiacetic acid |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6515168B1 (id) |
| EP (1) | EP1095048B1 (id) |
| CN (1) | CN1221557C (id) |
| AR (1) | AR019356A1 (id) |
| AT (1) | ATE263175T1 (id) |
| AU (1) | AU761569B2 (id) |
| BR (1) | BR9911949A (id) |
| CA (1) | CA2337111A1 (id) |
| DE (1) | DE69916067T2 (id) |
| ID (1) | ID27785A (id) |
| IE (1) | IES980552A2 (id) |
| MY (1) | MY125042A (id) |
| TW (1) | TWI243822B (id) |
| WO (1) | WO2000002888A1 (id) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1200944C (zh) * | 2001-01-12 | 2005-05-11 | 巴斯福股份公司 | N-膦酰基甲基亚氨基二乙酸的制备方法 |
| BRPI0610412A2 (pt) | 2005-04-25 | 2010-06-22 | Monsanto Technology Llc | alteração da distribuição de tamanho do cristal de ácido n-(fosfonometil)iminodiacético para filtração melhorada e qualidade do produto |
| CN100400543C (zh) * | 2006-09-08 | 2008-07-09 | 四川贝尔实业有限责任公司 | 亚氨基二乙腈水解制备双甘膦的方法 |
| CN102515385B (zh) * | 2011-11-29 | 2013-05-22 | 中国科学院南京土壤研究所 | 高钠盐废水除钠处理工艺及其装置 |
| PL2875037T4 (pl) | 2012-07-17 | 2017-06-30 | Straitmark Holding Ag | Sposób syntezy N-(fosfonometylo)glicyny |
| BR112015000988A2 (pt) | 2012-07-17 | 2017-06-27 | Straitmark Holding Ag | método para a síntese de ácido n-fosfonometiliminodiacético ou derivados do mesmo |
| BR112015000990B1 (pt) | 2012-07-17 | 2020-04-28 | Monsanto Technology Llc | Método para a síntese de um ácido aminoalquilenofosfônico ouseus ésteres fosfatos |
| EP2875035A1 (en) | 2012-07-17 | 2015-05-27 | Straitmark Holding AG | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2895989A (en) | 1956-06-22 | 1959-07-21 | Dow Chemical Co | Method for the preparation of iminodiacetic acid |
| US4002672A (en) | 1972-03-22 | 1977-01-11 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3950402A (en) * | 1972-05-31 | 1976-04-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3954848A (en) | 1972-05-31 | 1976-05-04 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3808269A (en) | 1972-12-29 | 1974-04-30 | Grace W R & Co | Process for recovering iminodiacetic acid from sodium sulfate solutions |
| US3904668A (en) | 1973-11-15 | 1975-09-09 | Grace W R & Co | Process for preparing iminodiacetonitrile and alkali metal iminodiacetates |
| US3969398A (en) | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| MX4703E (es) | 1976-12-20 | 1982-08-04 | Monsanto Co | Procedimiento mejorado para la preparacion de mono y disales de n-fosfonometilglicina |
| GB2148287B (en) | 1983-10-05 | 1987-04-15 | Nippon Catalytic Chem Ind | Preparation of aminocarboxylic acid salts from amino alcohols |
| US4724103A (en) * | 1984-02-27 | 1988-02-09 | Monsanto Company | Process for preparing N,N-diacetic acid aminomethylenephosphonic acid |
| US4775498A (en) | 1984-12-05 | 1988-10-04 | Monsanto Company | Process for preparing N,N-diacetic acid aminomethylenephosphonic acid |
| US4582650A (en) | 1985-02-11 | 1986-04-15 | Monsanto Company | Oxidation with encapsulated co-catalyst |
| US4579689A (en) | 1985-02-11 | 1986-04-01 | Monsanto Company | Oxidation with coated catalyst |
| US4696772A (en) | 1985-02-28 | 1987-09-29 | Monsanto Company | Amine oxidation using carbon catalyst having oxides removed from surface |
| HU200780B (en) | 1988-02-08 | 1990-08-28 | Nitrokemia Ipartelepek | Process for producing n-phosphonomethyl iminodiacetic acid from double salt of iminodiacetic acid |
| ES2021229A6 (es) | 1990-03-12 | 1991-10-16 | Ercros Sa | Perfeccionamientos introducidos en un procedimiento de obtencion de n-fosfonometilglicina por oxidacion de n-fosfonometiliminodiacetico. |
| US5095140A (en) | 1990-06-25 | 1992-03-10 | Monsanto Company | Peroxide process for producing N-phosphonomethylglycine |
| GB9300641D0 (en) | 1993-01-14 | 1993-03-03 | Zeneca Ltd | Process |
| US5312973A (en) | 1993-03-25 | 1994-05-17 | Finchimica S.P.A. | Process for producing n-phosphono-methyl-imino-diacetic acid |
| DK0694030T4 (da) | 1993-04-12 | 2003-03-03 | Monsanto Co | Fremgangsmåde til fremstilling af aminocarboxylsyresalte |
| EP0672765B1 (en) | 1994-03-14 | 1999-06-30 | Studiengesellschaft Kohle mbH | Electrochemical reduction of metal salts as a method of preparing highly dispersed metal colloids and substrate fixed metal clusters by electrochemical reduction of metal salts |
| US5689000A (en) | 1994-07-01 | 1997-11-18 | Monsanto Company | Process for preparing carboxylic acid salts and catalysts useful in such process |
| ATE213249T1 (de) | 1995-06-07 | 2002-02-15 | Monsanto Technology Llc | Verfahren zur herstellung von n- phosphonomethyliminodiessigesäure. |
| WO2000014093A1 (en) | 1998-09-08 | 2000-03-16 | Hampshire Chemical Corp. | Synthesis of phosphonomethyliminodiacetic acid with reduced effluent |
-
1998
- 1998-07-09 IE IE980552A patent/IES980552A2/en not_active IP Right Cessation
-
1999
- 1999-07-07 TW TW088111544A patent/TWI243822B/zh not_active IP Right Cessation
- 1999-07-08 DE DE69916067T patent/DE69916067T2/de not_active Expired - Fee Related
- 1999-07-08 AR ARP990103344A patent/AR019356A1/es active IP Right Grant
- 1999-07-08 AT AT99929654T patent/ATE263175T1/de not_active IP Right Cessation
- 1999-07-08 AU AU46430/99A patent/AU761569B2/en not_active Ceased
- 1999-07-08 EP EP99929654A patent/EP1095048B1/en not_active Expired - Lifetime
- 1999-07-08 ID IDW20010303A patent/ID27785A/id unknown
- 1999-07-08 BR BR9911949-8A patent/BR9911949A/pt not_active Application Discontinuation
- 1999-07-08 MY MYPI99002874A patent/MY125042A/en unknown
- 1999-07-08 CN CN99808354.2A patent/CN1221557C/zh not_active Expired - Fee Related
- 1999-07-08 US US09/743,380 patent/US6515168B1/en not_active Expired - Fee Related
- 1999-07-08 CA CA002337111A patent/CA2337111A1/en not_active Abandoned
- 1999-07-08 WO PCT/IE1999/000062 patent/WO2000002888A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BR9911949A (pt) | 2001-03-27 |
| WO2000002888A1 (en) | 2000-01-20 |
| DE69916067D1 (de) | 2004-05-06 |
| US6515168B1 (en) | 2003-02-04 |
| CN1308634A (zh) | 2001-08-15 |
| ATE263175T1 (de) | 2004-04-15 |
| MY125042A (en) | 2006-07-31 |
| EP1095048B1 (en) | 2004-03-31 |
| EP1095048A1 (en) | 2001-05-02 |
| DE69916067T2 (de) | 2004-12-30 |
| TWI243822B (en) | 2005-11-21 |
| AU761569B2 (en) | 2003-06-05 |
| ID27785A (id) | 2001-04-26 |
| AU4643099A (en) | 2000-02-01 |
| AR019356A1 (es) | 2002-02-13 |
| CA2337111A1 (en) | 2000-01-20 |
| CN1221557C (zh) | 2005-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |